Best apartment offers in Chicago, IL

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Chicago, IL apartments
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13595 Holiday apartments in Chicago, IL

Best family friendly Chicago, IL Holiday Apartments and Self Contained Accommodations

Among the 13595 accommodations in Chicago, IL, here are the 4 best family friendly holiday apartments

Designer Hideaway Private Patio Near Wicker Park - Chicago, IL
9.3 3 reviews

Designer Hideaway Private Patio Near Wicker Park

apartment, Chicago
This Chicago flat is situated 3.9 kilometres from the United Centre, providing easy access to downtown attractions within a 6.4 kilometre radius, including Union Station and Water Tower Chicago.
This 74 square metre flat accommodates up to nine guests, offering a fully equipped kitchen with a dishwasher and oven, free WiFi, air conditioning, on-site laundry, complimentary parking, and a private patio, all within a non-smoking environment.
Chic And Charming Vintage Condominium In Lincoln Park - Chicago, IL
9.7 414 reviews

Chic And Charming Vintage Condominium In Lincoln Park

apartment, Chicago
This three-bedroom Lincoln Park flat, situated approximately 5km from downtown Chicago and Wrigley Field, offers easy access to local attractions such as Pequod's Pizza and Sweet Mandy B's.
The property boasts a well-equipped kitchen, two bathrooms (one with a jacuzzi bath), a private balcony with city views, and gated parking for two cars, comfortably accommodating up to six guests.
Beautiful & Inspiring Three Bedroom Home In Roscoe Village - Chicago, IL
9.8 475 reviews

Beautiful & Inspiring Three Bedroom Home In Roscoe Village

apartment, Chicago
This three-bedroom Chicago apartment, ideal for families, is situated in Roscoe Village, a 1.4 km walk from the Paulina–Lincoln/Roscoe Brown Line station, 1.6 km from Wrigley Field, and 8 km from Chicago's city centre.
The 3-bathroom property sleeps five, boasts a full kitchen with dishwasher, high-speed internet, and a flexible office space convertible to a child's room; nearby attractions include Wrigley Field and easy access to downtown Chicago via public transport.
Modern 2br In Roscoe/wrigley With Free Street Parking Walk To Paulina Brown-line - Chicago, IL
10 2 reviews

Modern 2br In Roscoe/wrigley With Free Street Parking Walk To Paulina Brown-line

apartment, Chicago
This Roscoe Village/Lake View flat is conveniently located a 5-minute walk from the Brown Line Paulina station, a 20-minute walk from Wrigley Field, 4.8km from Lake Michigan beaches, and 8km from Chicago's city centre.
The 84-square-metre, two-bedroom, one-bathroom apartment sleeps four, boasting a chef's kitchen, private patio with Weber grill, fast WiFi, and on-street parking (garage parking available for a fee), alongside a 60" Roku TV and in-unit laundry facilities.

Best Chicago, IL holiday apartments with a balcony

Top Floor Views + Central Comfort - Chicago, IL
No reviews

Top Floor Views + Central Comfort

apartment, Chicago
This top-floor flat in Chicago offers exceptional city views and is situated just 400 metres from Union Station and 800 metres from the Willis Tower.
This modern apartment accommodates up to six guests with two bedrooms and two bathrooms, featuring a designer kitchen with premium appliances, a 75-inch television, and access to building amenities including a fitness centre, game room, and an outdoor sky terrace with grills and firepits.
Elegant 2br With Resort Amenities & City Views - Chicago, IL
10 5 reviews

Elegant 2br With Resort Amenities & City Views

apartment, Chicago
This Magnificent Mile flat, near Washington Square Park and the Museum of Contemporary Art in downtown Chicago, offers easy access to Michigan Avenue's shops and iconic landmarks such as the Water Tower.
The 110 square metre dwelling boasts two bedrooms with queen-size beds, two bathrooms, and sleeps up to seven guests, featuring a high-end kitchen, private balcony, and access to a building with a pool, hot tub, fitness centre, and rooftop sky club.
Sky-high 2br W/ Gym & City Views - Chicago, IL
No reviews

Sky-high 2br W/ Gym & City Views

apartment, Chicago
This Downtown Chicago flat is conveniently located less than 1.6km from Union Park and the United Centre, and within 3.2km of the Chicago Riverwalk and Michigan Avenue.
The 125 square metre, two-bedroom, two-bathroom apartment sleeps five, boasting a fully equipped kitchen, in-unit laundry, private balcony, and access to a swimming pool, fitness centre, and concierge services.
This 2 Bedroom 2 Bathroom Elegantly Furnished Home Is Ready For All Your Needs.  Featuring A Primary Bedroom Suite, Tv Room, Dining Room, And Additional Sitting Areas. - Chicago, IL
10 15 reviews

This 2 Bedroom 2 Bathroom Elegantly Furnished Home Is Ready For All Your Needs. Featuring A Primary Bedroom Suite, Tv Room, Dining Room, And Additional Sitting Areas.

apartment, Chicago
This Rogers Park flat, three blocks from Lake Michigan (approx. 0.5km) and 2.4km from Loyola University Chicago, offers easy access to Rogers Park's amenities and public transport links to downtown Chicago, Navy Pier, and Grant Park.
The spacious two-bedroom apartment sleeps four, features a fully equipped kitchen with a KitchenAid stand mixer, two updated bathrooms (one with a jetted tub, one with a bidet), and family-friendly amenities including a highchair and crib, plus complimentary laundry facilities.

Frequently asked questions about apartment rentals in Chicago, IL

  • What are the must-see attractions for a 2 days stay in Chicago, IL?

    For a two-day trip, you can't miss the iconic Willis Tower (formerly Sears Tower) for panoramic views of the city. Then, explore Millennium Park, home to Cloud Gate, nicknamed 'The Bean', and the Crown Fountain with its interactive water displays. Finally, stroll along Navy Pier for its Ferris wheel, shops, and restaurants.
  • What are the best apartments in Chicago, IL?

  • Which neighborhoods in Chicago, IL are best for renting an apartment?

    For a vibrant, walkable neighbourhood, consider Lincoln Park with its green spaces and Lake Michigan access. If you prefer a more historic feel, try the Gold Coast, known for its elegant architecture. For a more affordable option with great restaurants and nightlife, check out Wicker Park.
  • What are the best apartments with a pool in Chicago, IL?

  • What are the top cultural and historical sites in Chicago, IL?

    Chicago is brimming with cultural and historical gems. The Art Institute of Chicago houses masterpieces by Monet and Van Gogh, while the Field Museum boasts dinosaur skeletons and ancient Egyptian artefacts. For a taste of history, visit the Chicago Cultural Center, a stunning building with free concerts and exhibitions, or the Museum of Science and Industry.
  • What are the best apartments with a jacuzzi in Chicago, IL?

  • What makes Chicago, IL unique or famous?

    Chicago is known for its stunning architecture, from the towering skyscrapers of the Loop to the charming brownstones of the Gold Coast. It's also a culinary powerhouse, with world-class restaurants and a renowned deep-dish pizza scene. And don't forget the vibrant arts and culture scene, with world-class museums, theatres, and music venues.
  • What are the best apartments for families and kids in Chicago, IL?

  • Where can you find the best local markets and street food in Chicago, IL?

    For a taste of Chicago's diverse food scene, head to Maxwell Street Market on Sundays for a mix of local produce, crafts, and street food. The Wicker Park Farmers Market on Saturdays offers fresh, seasonal produce, while the Green City Market in Lincoln Park has a wide selection of local vendors.
  • What are the best pet friendly apartments in Chicago, IL?

  • How is the public transportation system in Chicago, IL?

    Chicago has a reliable and extensive public transportation system, the 'L', which is a combination of elevated trains and underground subway lines. It's a great way to get around the city, especially during rush hour. You can also use the CTA buses for more local travel.
  • What are the best apartments with parking in Chicago, IL?

  • Which seasonal events or festivals should apartment renters look forward to in Chicago, IL?

    Chicago is a city that comes alive with seasonal events. In the spring, enjoy the Chicago Blues Festival, while summer brings the Taste of Chicago food festival. Autumn is perfect for the Chicago Marathon, and winter offers festive holiday markets and ice skating at Millennium Park.
  • What amenities are typically included in apartments in Chicago, IL?

    Apartments in Chicago typically include central heating and air conditioning, in-building laundry facilities, and sometimes a gym or a rooftop terrace. Some newer buildings may also offer amenities like a swimming pool, a dog park, or a resident lounge.
  • What leisure activities are available for relaxation in Chicago, IL?

    For relaxation, Chicago offers a variety of options. You can stroll along the Lakefront Trail for stunning views of Lake Michigan, visit the Lincoln Park Zoo for a free day out, or take a boat tour on the Chicago River. For a quieter experience, explore the Garfield Park Conservatory, a beautiful greenhouse with exotic plants.

Popular destinations

Best Chicago, IL holiday apartments with parking

Inspiring Stone Grotto Sleeps 10-20 & Free Parking - Chicago, IL
9.9 260 reviews

Inspiring Stone Grotto Sleeps 10-20 & Free Parking

apartment, Chicago
This spacious four-bedroom apartment is situated in East Lakeview, just two blocks from Lake Michigan and Lincoln Park, offering easy access to the city's attractions and public transport. It has consistently received excellent ratings for location, cleanliness and overall experience.
The property is a unique blend of modern amenities and historical charm, housed in a historic 1893 building. Guests can enjoy the fully equipped kitchen, large TV, Wi-Fi, a private garage, and a spacious backyard, perfect for relaxing or enjoying outdoor activities.
2 Bedroom 3 Beds  1 Bath Apartment In Berwyn - Chicago, IL
9.7 167 reviews

2 Bedroom 3 Beds 1 Bath Apartment In Berwyn

apartment, Berwyn
This Berwyn apartment is conveniently situated on Route 66, a short 1.6-2.4 km walk from the Metra station providing easy access to Chicago, and within walking distance of local restaurants, auto repair shops, and a Walgreens.
The two-bedroom, one-bathroom flat sleeps up to six guests comfortably, thanks to an inflatable bed, and boasts a fully equipped kitchen, air conditioning, parking, and internet access; its photo-ready interior is also perfect for personal photoshoots.
Stylish Living Area And Indoor Gym - Chic Urban Escape - Chicago, IL
No reviews

Stylish Living Area And Indoor Gym - Chic Urban Escape

apartment, Chicago
This 2-bedroom flat is located in a central Chicago district, offering convenient access to Millennium Park, Navy Pier, and the Riverwalk, all within 1.5 kilometres.
This family-friendly accommodation for up to 7 guests features a fully equipped kitchen with a dishwasher, air conditioning, an on-site indoor gym, and multiple parking options, with keyless entry and an on-site washer and dryer for added convenience.
Cheerful 3 Bedroom. Feels Like Home. - Chicago, IL
9.6 28 reviews

Cheerful 3 Bedroom. Feels Like Home.

apartment, Dunning
This Dunning family home, situated approximately 9.7 kilometres from the Frank Lloyd Wright Historic District and Copernicus Centre, offers easy access to Milwaukee Avenue's amenities.
Sleeping six guests, this three-bedroom, two-bathroom property boasts a fully equipped kitchen, private patio, free Wi-Fi, and parking; nearby attractions include the Fashion Outlets of Chicago.

Neighborhoods and points of interest in Chicago, IL

Best Chicago, IL holiday apartments with air conditioning

Explore Chicago From Our Trendy Wicker Park Airbnb - Chicago, IL
9.7 138 reviews

Explore Chicago From Our Trendy Wicker Park Airbnb

apartment, Chicago
This Chicago apartment rental is situated near Kasama, a Michelin-starred restaurant, in a convenient location, only a short distance away.
The two-bedroom, one-bathroom flat sleeps five guests comfortably, boasting a fully equipped kitchen, 55-inch TV, and a spacious master bedroom with a walk-in closet; a pull-out sofa provides extra sleeping space.
Modern Gazebo Sleeps 17 Birthday Anniversary - Chicago, IL
9.9 157 reviews

Modern Gazebo Sleeps 17 Birthday Anniversary

apartment, Chicago
This six-bedroom apartment is located just outside downtown Chicago, within easy reach of popular neighbourhoods like Lakeview, Wrigleyville, and Logan Square, and is a short drive from both downtown and O'Hare Airport. It has received excellent user ratings for location, cleanliness, and overall experience.
The apartment comfortably sleeps 14 guests across its six bedrooms and four bathrooms. It offers a range of amenities including a fully equipped kitchen, a private patio and gazebo, a gated driveway, and a lower level family area, making it ideal for large groups or families.
Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied - Chicago, IL
8.8 11 reviews

Luxe Vintage Loft, 10min To Downtown, Retro Movie Theatre - 15% Discount Applied

apartment, Chicago
This spacious Chicago apartment, ideal for families or groups, is situated in New City, offering easy access to Lake Michigan, Grant Park, and major museums such as the Art Institute of Chicago and the Field Museum (distances unspecified).
Sleeping 8-12 guests, the three-bedroom, three-bathroom property boasts a fully equipped kitchen, themed rooms (including a retro cinema and galaxy kids' room), smart TVs, high-speed Wi-Fi, and family-friendly amenities like cribs and high chairs, alongside a garden, spa and parking.
Historic Pullman/color Splash/great Neighborhood - Chicago, IL
9.6 152 reviews

Historic Pullman/color Splash/great Neighborhood

apartment, Chicago
This Pullman, Chicago apartment is situated near the expressway, a 32km drive from the city centre, and a 10-minute walk from the Metra train station offering a 30-minute commute downtown.
The two-bedroom, one-bathroom flat sleeps four, features a fully equipped kitchen with fridge and microwave, air conditioning, parking, a garden, and is within easy reach of local restaurants, cafes, and a Walmart.
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